Vice President of Information Technology

Olympus Insurance Company • Jacksonville, FL

20h

About The Position

The Vice President of Information Technology is responsible for leading Olympus Insurance Company’s enterprise technology strategy, governance, and execution across all IT functions. This role ensures alignment between technology initiatives and business objectives, enabling scalable growth, operational efficiency, security, and long-term sustainability.
The VP of IT serves as a key member of the Executive Leadership Team, contributing to enterprise-wide strategy, decision-making, and organizational performance. This role requires a business-oriented technology leader who can operate above day-to-day delivery while ensuring disciplined execution, strong governance, and measurable outcomes.
This role oversees application delivery, infrastructure, cybersecurity, data and analytics, governance, and IT service delivery, while aligning technology investments with organizational priorities and financial objectives.

Requirements

• Bachelor’s degree in Information Technology, Computer Science, or related field required (Master’s preferred)
• 12+ years of progressive IT leadership experience, including senior or executive roles
• Proven experience leading multi-functional IT organizations across operations, development, and architecture
• Experience in insurance, financial services, or other regulated industries strongly preferred
• Demonstrated success leading enterprise technology strategy and transformation initiatives
• Strong understanding of IT operations, SDLC, DevOps, cybersecurity, infrastructure, and enterprise architecture
• Experience establishing governance models, prioritization frameworks, and delivery discipline
• Knowledge of data governance and analytics frameworks
• Strong financial acumen including budgeting, forecasting, and ROI analysis
• Experience managing complex vendor ecosystems and contracts
• Executive presence with the ability to influence and partner across leadership teams
• Strong people leadership with demonstrated success managing and developing senior leaders
• Strategic thinker with the ability to translate vision into execution
• Ability to lead change, drive accountability, and deliver results in a fast-paced environment
• Excellent communication skills, with the ability to translate complex technical concepts into business terms

Responsibilities

• Serve as an active member of the Executive Leadership Team, contributing to enterprise strategy, planning, and decision-making
• Act as a trusted advisor to executive leadership on technology opportunities, risks, and tradeoffs
• Partner with senior leaders across Claims, Underwriting, Finance, HR, and Operations to align technology initiatives with business priorities
• Translate business strategy into a clear, actionable technology roadmap that supports scalability, efficiency, and service delivery
• Define and own the enterprise technology strategy and roadmap aligned with business and financial objectives
• Establish governance frameworks for demand intake, prioritization, and change management
• Ensure alignment between business priorities and technology execution across the organization
• Oversee application development, production support, and ongoing enhancements
• Ensure disciplined execution across requirements, QA, release management, and delivery processes
• Drive predictable delivery while balancing speed, quality, and long-term sustainability
• Provide executive oversight across application delivery, infrastructure, cybersecurity, data and analytics, governance, and IT service delivery
• Maintain accountability for enterprise architecture and overall technology direction
• Ensure systems, integrations, and data flows are designed intentionally and consistently
• Guide platform selection, modernization, and integration strategies
• Ensure architectural decisions support scalability, reliability, and maintainability
• Own the enterprise data, analytics, and reporting strategy
• Ensure business leaders have access to accurate, timely, and actionable data
• Promote strong data governance, quality, and reporting consistency across the organization
• Ensure reliable, secure, and scalable enterprise infrastructure
• Oversee cloud environments, network operations, system performance, and incident response
• Own cybersecurity strategy, risk management, and remediation efforts
• Ensure appropriate controls for identity, access, and data protection
• Own the creation, maintenance, and enforcement of IT policies, including: Information security Data governance and classification Acceptable use standards Incident response, disaster recovery, and business continuity
• Ensure alignment with regulatory requirements and industry standards
• Drive organization-wide awareness and compliance with IT policies
• Lead, coach, and develop a team of IT Directors and senior leaders
• Establish clear performance expectations, accountability, and decision-making structures
• Conduct ongoing performance management, including goal setting, feedback, and development planning
• Build leadership capability and succession planning within the IT organization
• Strengthen organizational maturity by reducing reliance on key individuals through process, documentation, and structure
• Own IT budget, forecasting, and cost optimization efforts
• Manage vendor relationships, contracts, and licensing
• Ensure technology investments are supported by cost-benefit analysis and deliver measurable business value
• Optimize vendor portfolio to support strategic and operational goals
• Lead enterprise technology initiatives including digital transformation, AI adoption, and automation
• Evaluate emerging technologies and identify opportunities to improve efficiency and business outcomes
• Ensure disciplined execution of high-impact, cross-functional initiatives

Benefits

• Employer-sponsored medical, dental, and vision plans
• Company-paid life insurance, short-term disability, and long-term disability
• 401(k) with company match
• Paid Time Off to include annual PTO, Holidays, Floating Holidays, and Volunteer Time Off
• Education Assistance Program and ongoing professional development opportunities
• Wellness Lunch N Learns
• Employee perks such as pet insurance, discount programs, and a welcoming office environment

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Number of Employees: 11-50 employees